Pyridine-derivatives

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 944401-56-3, name is 5-Bromo-4-(trifluoromethyl)pyridin-2-amine. A new synthetic method of this compound is introduced below., name: 5-Bromo-4-(trifluoromethyl)pyridin-2-amine

To a dry flask was added 5-bromo-4-(trifluoromethyl)pyridin-2-amine (2200.91 mmol), potassium acetate (446 mg, 4.55 mmol), bis(pinacolato)diboron (279 mg,1.10 mmol, 1.1 eq.) and dioxane (5 mL). N2 was bubbled through the solution for 1.5 minutes, at which time 1 ,1- bis(diphenylphosphino)ferrocene-palladium(II) (32 mg, 45iimol) was added. The reaction was stirred at 100 C for 16 hours under N2. After cooling to room temperature, the dioxane was removed in vacuo. EA was added and the resulting slurry was sonicated and filtered. Additional ethyl acetate was used to wash the solid. The combined organic was concentrated and the crude material was purified by silica gel chromatography using Petroleum ether : Ethyl acetate (10:1) affording to compound 30 (60 mg, 23%) as a light yellow solid. ?H NMR (400 MHz, CDC13): 8.47 (s, 1H), 6.76 (s, 1H), 5.15 (bs, 2H), 1.34 (s, 12H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 944401-56-3, 5-Bromo-4-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; SUZHOU KINTOR PHARMACEUTICALS, INC.; GUO, Chuangxin; TONG, Youzhi; (160 pag.)WO2017/219800; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1346575-64-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1346575-64-1, name is 3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-one, molecular formula is C10H16N2O, molecular weight is 180.25, as common compound, the synthetic route is as follows.

Example 11l-(l-Methylethyl)- V-[(6-methyl-2-oxo-4-propyl-l,2-dihydro-3-pyridinyl)methyl]-6-(4- pyridinyl)-l -pyrazolo[3,4-6]pyridine-4-carboxamidel-(l-Methylethyl)-6-(4-pyridinyl)-l H-pyrazolo [3, 4-b]pyridine-4-carboxylic acid (150 mg, 0.531 mmol), 3-(aminomethyl)-6-methyl-4-propyl-2(lH)-pyridinone (1 15 mg, 0.531 mmol), EDC (122 mg, 0.638 mmol), HOAt (72.3 mg, 0.531 mmol), and N- methylmorpholine (0.233 mL, 2.12 mmol) were suspended in DMF (5 mL) and stirred at room temperature overnight, water was added to the reaction mixture, and the contents were filtered. The filter cake was washed with addional water (2x). The crude solid was purified by reverse phase HPLC (mobile phase: 10-30% ACN in H20, 0.1% TFA). The isolated solid was then neutralized with saturated NaHC03, and washed with EtOAc (5 x 15 mL). The combined organic layers were dried over Na2S04, filtered, and concentrated in vacuo to afford the title compound as an off-white solid, 0.060 g (24%). LCMS E-S (M+H) = 445.3. 1H NMR (400 MHz, DMSO-d6) ? ppm 0.84 – 0.92 (m, 3 H), 1.47 – 1.54 (m, 2 H), 1.57 (d, J=6.82 Hz, 6 H), 2.14 (s, 3 H), 2.48 – 2.52 (m, 2 H), 4.42 – 4.49 (m, 2 H), 5.33 – 5.43 (m, 1 H), 5.90 – 5.96 (m, 1 H), 8.28 – 8.37 (m, 3 H), 8.44 – 8.48 (m, 1 H), 8.82 – 8.87 (m, 2 H), 8.99 – 9.04 (m, 1 H), 11.58 (s, 1 H).

Statistics shows that 1346575-64-1 is playing an increasingly important role. we look forward to future research findings about 3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-one.

Reference:
Patent; GLAX0SMITHKLINE LLC; BURGESS, Joelle, Lorraine; JOHNSON, Neil, W.; KNIGHT, Steven, David; LAFRANCE, Louis, Vincent, III; MILLER, William, H.; NEWLANDER, Kenneth, Allen; ROMERIL, Stuart, Paul; ROUSE, Meagan, B.; SUAREZ, Dominic; TIAN, Xinrong; VERMA, Sharad, Kumar; WO2013/39988; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 142266-62-4, 2,5,6-Trichloronicotinamide, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Application In Synthesis of 2,5,6-Trichloronicotinamide, blongs to pyridine-derivatives compound. Application In Synthesis of 2,5,6-Trichloronicotinamide

Step 2: 2,5,6-Trichloro-N-((2-ethyl-4-methylpyridin-3-yl)carbamoyl)nicotinamide To a solution of 2,5,6-trichloronicotinamide (Intermediate P, 2.5 g, 11.1 mmol) in THF (20 mL) was added oxalyl chloride (2 M solution in DCM, 5.4 mL, 10.8 mmol) slowly via syringe. The resulting mixture was heated at 65 C. for 1.5 h, then heating was stopped and the reaction was allowed to cool to room temperature. A solution of 2-ethyl-4-methylpyridin-3-amine (Intermediate W, 1.5 g, 10.7 mmol) in THF (15 mL) was added via cannula. The resulting mixture was stirred at room temperature for 1 h, and then was partially concentrated to remove most of the THF. The residue was partitioned between saturated aqueous sodium bicarbonate (30 mL) and EtOAc (50 mL). The organic layer was washed with brine (1*), dried over anhydrous sodium sulfate and concentrated. The residue was suspended in 10:1 heptane/EtOAc (60 mL) and filtered to provide 2,5,6-trichloro-N-((2-ethyl-4-methylpyridin-3-yl)carbamoyl)nicotinamide. The product was carried on directly into the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,142266-62-4, 2,5,6-Trichloronicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; KOPECKY, David John; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; BOOKER, Shon; NISHIMURA, Nobuko; SHIN, Youngsook; TAMAYO, Nuria A.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; (266 pag.)US2018/334454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 68325-15-5, Adding some certain compound to certain chemical reactions, such as: 68325-15-5, name is 3-Chloro-4-cyanopyridine,molecular formula is C6H3ClN2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 68325-15-5.

Step B: Preparation of 3-(2-(trimethylsilyl)ethoxy)isonicotinonitrile: A flask was charged with 2-(trimethylsilyl)ethanol (1.02 g, 8.66 mmol) and added THF (20 mL). Sodium hydride (0.219 g, 8.66 mmol) was added and the reaction was stirred at ambient temperature for 1 hour. 3-Chloroisonicotinonitrile (1.00 g, 7.22 mmol) was added, and the reaction mixture was stirred at ambient temperature for 1 hour and then at 50 0C overnight. A saturated solution of ammonium chloride was added. The reaction mixture was extracted with ethyl acetate, dried and concentrated to give the desired product (1.30 g, 81.7% yield) as light brown semi solid material.

According to the analysis of related databases, 68325-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2008/91770; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 33674-96-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 33674-96-3, name is (6-Bromopyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of ( 6-bromopyridin-2-yl) methanol (5.22 g) , PPh3 (8.74 g) and benzotrifluoride (210 mL) was added tetrabromomethane (11.1 g) at 0C. The mixture was stirred at 0C for 2 hr, and the insoluble substance was removed by filtration, and washed with ethyl acetate/diethyl ether. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (7.33 g) . XH NMR (300 MHz, CDCI3) delta 4.50 (2H, s) , 7.39-7.45 (2H, m) , 7.52-7.60 (1H, m) .

According to the analysis of related databases, 33674-96-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAJITA, Yuichi; MIKAMI, Satoshi; MIYANOHANA, Yuhei; KOIKE, Tatsuki; DAINI, Masaki; OYABU, Norio; OGINO, Masaki; TAKEUCHI, Kohei; ITO, Yoshiteru; TOKUNAGA, Norihito; SUGIMOTO, Takahiro; MIYAZAKI,Tohru; ODA, Tsuneo; HOASHI, Yasutaka; HATTORI,Yasushi; IMAMURA, Keisuke; (413 pag.)WO2019/27058; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 50720-12-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 50720-12-2, name is 3-Bromo-5-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: 3-Formyl-5-methoxypyridine; [00338] To a solution of 3-Bromo-5-methoxypyridine (2.5g, 13.3 mmol) in anhydrous diethyl ether cooled to – 100 0C was added n-butyllithium (2.5M soln in hexanes: 5.85 mL, 14.6 mmol) dropwise whilst maintaing an internal temperature <-94 0C. After subsequent stirring for 30 minutes, anhydrous DMF (1.34 mL, 17.3 mmol) was added and the reaction mixture allowed to warm to -60 0C. The solution was then poured into sat'd. aq. NaCl soln. and extracted with diethyl ether (3 x 100 mL), the ethereal phase dried (K2CO3), filtered and evaporated in vacuo. The residue was purified on silica gel eluting with a gradient of 0 to 30% EtOAc in hexanes to afford the title material as an oil. While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 50720-12-2, 3-Bromo-5-methoxypyridine. Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; WO2007/47207; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 2002-04-2, Adding some certain compound to certain chemical reactions, such as: 2002-04-2, name is 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine,molecular formula is C7H6N4S, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2002-04-2.

General procedure: 2-Amino-5-(4-pyridinyl)-1,3,4-thiadiazole (0.057 g, 0.32 mmol) was mixed with 3,4-dichlorophenyl isocyanate (0.050 g, 0.027 mmol), dissolved in DMF (1 mL), and heated at 90C for 30 min. The mixture was allowed to cool before quenching with DI water (1 mL) to yield a precipitate.

According to the analysis of related databases, 2002-04-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rosenthal, Andrew S.; Dexheimer, Thomas S.; Gileadi, Opher; Nguyen, Giang H.; Chu, Wai Kit; Hickson, Ian D.; Jadhav, Ajit; Simeonov, Anton; Maloney, David J.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 20; (2013); p. 5660 – 5666;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67346-74-1 , The common heterocyclic compound, 67346-74-1, name is 3-Ethynylpyridin-2-amine, molecular formula is C7H6N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Reference Example 64 3-(3-(3-Phenoxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine; To a tetrahydrofuran (10.0 mL) solution of (3-phenoxy-phenyl)-acetohydroximoyl chloride (150 mg, 0.573 mmol) described in Manufacturing Example 64-1-3 and 3-ethynyl-pyridin-2-ylamine (30.0 mg, 0.254 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (106 muL, 0.762 mmol) at room temperature, which was stirred for 2 hours at 60° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate_heptane=1:2), the mixture was further purified by reverse-phase high-performance liquid chromatography (using an acetonitrile-water mobile phase containing 0.1percent trifluoracetic acid) to obtain the title compound (6.6 mg, 43percent) as a trifluoracetic acid salt.MS m/e(ESI) 344.07(MH+)1H-NMR Spectrum (CD3OD) delta (ppm): 4.08 (2H, s), 6.81 (1H, s), 6.85-6.87 (1H, m), 6.96-6.98 (3H, m), 7.03-7.12 (3H, m), 7.29-7.36 (3H, m), 8.03-8.04 (1H, m), 8.32-8.34 (1H, m).

The synthetic route of 67346-74-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7598-35-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 7598-35-8, name is 2-Bromopyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Under the protection of nitrogen, 0.69g (4.00mmol) 2-bromo-4-aminopyridine, 1.02g (6.40mmol) 2, 6-difluoro-3-boronic acid pyridine, 0.28g (0.24mmol) Pd (PPh 3) 4 soluble in 25mLTHF aqueous solution, add 10 ml of the mass fraction of 5% of K 2 CO 3 aqueous solution, heating to 70 C reflux state, the stirring reaction 18h. After the natural cooling to room temperature, adding proper amount of distilled water, many times proper amount of ethyl acetate extraction. Combined with the phase, anhydrous MgSO 4 drying. Filtration, filtrate under reduced pressure, the crude product obtained after evaporating solvent. Using ethyl acetate: hexane (v/v) =1 […] 5 as eluant the separation by silica gel column chromatography, to obtain colourless solid product 0.26g, the yield is 63.0%.

According to the analysis of related databases, 7598-35-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ocean’s king lighting science & technology co. ltd; SHENZHEN OCEAN’S KING LIGHTING SCIENCE & TECHNOLOGY CO., LTD; Zhou, Mingjie; Wang, Ping; Zhang, Juanjuan; Liang, Lusheng; (17 pag.)CN103173209; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4021-11-8, Adding some certain compound to certain chemical reactions, such as: 4021-11-8, name is 2-Methylisonicotinic acid,molecular formula is C7H7NO2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4021-11-8.

a) A suspension of 2-methyl-pyridine-4-carboxylic acid (1.0 g, 7.29 mmol) in methanol (50 mL) and H2SO4 (0.5 mL) is heated to 70 C. The solid material dissolves and stirring is continued at 70 C. for 18 h. The mixture is cooled to rt, filtered, and the filtrate is evaporated. The remaining solid is washed with diethyl ether and dried to give methyl 2-methyl-pyridine-4-carboxylate; LC-MS: tR=0.39 min, [M+1]+=152.05.

According to the analysis of related databases, 4021-11-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bolli, Martin; Lescop, Cyrille; Mathys, Boris; Mueller, Claus; Nayler, Oliver; Steiner, Beat; Velker, Jorg; US2011/212998; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem